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R3255

Sigma-Aldrich

13-cis-Retinoic acid

≥98% (HPLC)

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Synonym(s):
Isotretinoin
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
EC Number:
MDL number:
PubChem Substance ID:

Assay

≥98% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

yellow to yellow-orange

mp

172-175 °C (lit.)

storage temp.

−20°C

SMILES string

[H]\C(C(O)=O)=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C

InChI

1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-

InChI key

SHGAZHPCJJPHSC-XFYACQKRSA-N

Gene Information

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This Item
PHR1188R4643R5754
13-cis-Retinoic acid ≥98% (HPLC)

Sigma-Aldrich

R3255

13-cis-Retinoic acid

Isotretinoin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1188

Isotretinoin

9-cis-Retinoic acid ≥98% (HPLC)

Sigma-Aldrich

R4643

9-cis-Retinoic acid

9-cis-Retinal vitamin A analog

Sigma-Aldrich

R5754

9-cis-Retinal

form

powder

form

-

form

powder

form

powder

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

color

yellow to yellow-orange

color

-

color

light yellow to yellow-orange

color

yellow to yellow-orange

mp

172-175 °C (lit.)

mp

172-175 °C (lit.)

mp

189-190 °C

mp

56-58 °C (lit.)

storage temp.

−20°C

storage temp.

-10 to -25°C

storage temp.

−20°C

storage temp.

−20°C

Application

13-cis-Retinoic acid has been used:
  • as a component of fresh media for LA-N-5 differentiation
  • to treat medulloblastoma cells for cell differentiation
  • to treat spheroids for generating time-lapse videos
  • to examine its head- deforming activity under light and dark conditions in Xenopus laevis

Biochem/physiol Actions

13-cis-Retinoic acid (RA) has anti-inflammatory and anti-tumor action. The action of RA is mediated through RAR-β and RAR-α receptors. RA attenuates iNOS expression and activity in cytokine-stimulated murine mesangial cells. It induces mitochondrial membrane permeability transition, observed as swelling and as a decrease in membrane potential, and stimulates the release of cytochrome c implicating mechanisms through the apoptosis pathway. These activities are reversed by EGTA and cyclosporin A. RA also increases MMP-1 protein expression partially via increased transcription.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Classifications

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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T1503
Product Number
-
25G
Pack Size/Quantity

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705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

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Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

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9-cis-Retinal vitamin A analog

Sigma-Aldrich

R5754

9-cis-Retinal

trans-Retinoic Acid Potent modulator of growth and differentiation. Inhibits melanocyte adhesion, motility, and growth.

Millipore

554720

trans-Retinoic Acid

Tretinoin United States Pharmacopeia (USP) Reference Standard

USP

1674004

Tretinoin

M P Rigobello et al.
Biochemical pharmacology, 58(4), 665-670 (1999-07-21)
Retinoic acids, structurally related to vitamin A, inhibit the in vitro proliferation of different types of normal and neoplastic cells. The effects of all-trans, 9-cis, and 13-cis retinoic acids were tested on mitochondria isolated from rat liver. All the compounds
Differential expression, distinct localization and opposite effect on Golgi structure and cell differentiation by a novel splice variant of human PRMT5
Sohail M , et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1853(10), 2444-2452 (2015)
Live multicellular tumor spheroid models for high-content imaging and screening in cancer drug discovery
Reid B G, et al.
Current Chemical Genomics and Translational Medicine, 8(Suppl-1), 27-27 (2014)
Raoud Marayati et al.
Translational oncology, 14(1), 100893-100893 (2020-10-04)
Retinoic acid (RA) therapy has been utilized as maintenance therapy for high-risk neuroblastoma, but over half of patients treated with RA relapse. Neuroblastoma stem cell-like cancer cells (SCLCCs) are a subpopulation of cells characterized by the expression of the cell
Induction of pronephric tubules by activin and retinoic acid in presumptive ectoderm of Xenopus laevis
Moriya N, et al.
Development, Growth & Differentiation, 35(2), 123-128 (1993)

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